Those Autofellatio Blues Ch. 01

She shook my hand, "I don't know if you remember me, I'm Elaine." She looked me up and down. "You've gotten so big! And so handsome!" She was smiling at me, and I liked it. She was very attractive, in a sweet, wholesome way. Her reddish hair was piled up in a bun, she wore a light blue blouse and khakis, and when she smiled her dark brown eyes glowed with merriment. I couldn't see how this nice lady could be involved in my punishment.

My mom checked her watch. "I have some errands to run. Is three hours enough?"

"Oh, that should be plenty of time."

"Then I'll be going." Mom looked at me. "You do everything Elaine tells you. Everything. Remember, you're being punished." And she turned and walked down the steps to the car, leaving me totally flabbergasted.

"Come inside, honey," Elaine said.

"Wait, what's going on?"

Elaine showed me that sweet smile. "Come inside and find out."

Mom was glaring at me from the car, so I obeyed. I was nervous. I didn't know this woman at all, and now I was following her up the stairs in this unfamiliar house.

"Can I get you something to drink, honey?" she asked.

"Um, no, no thanks."

Elaine took my hand and let me to the couch. Her hands were warm and soft. She had long pink fingernails, and despite my nervousness I was getting turned on.

My jaw wobbled up and down, but no words came out. "And she said you were cornholing yourself with some kind of stick."

Hearing the words "blowjob" and "cornhole" come from the lips of this motherly woman absolutely stunned me. Finding out that she knew about my hidden shame was worse. "My...my mother told you about that?"

Elaine smiled. "She did. Oh, don't be embarrassed!"

"Don't be embarrassed!? My mother told you...what she told you, and I shouldn't be embarrassed?"

"No," she said soothingly. "You should be proud of yourself!"

I was incredulous. "Proud?"

"Of course! Any boy would masturbate orally if he could, but how many boys have the athletic ability and physical endowment to do it?"

"So, you don't think I'm a pervert?"

"Not at all!"

"Well, I do. I think I'm sick to do that?"

She touched me on the arm. "Danny, are you gay?"

"No!"

"It's OK if you are. I have quite a few gay friends."

"I'm not gay. I like girls."

"So, you don't want to do what you do to other boys."

"No!"

"Do you think about girls when you're giving yourself pleasure?"

"Yes."

She nodded. "Then that's OK. That's fine. And you aren't a pervert. You aren't hurting anyone else, are you? You're just making yourself feel good in an unusual way."

She had this oddly soothing effect on me, probably because she was telling me what I wanted to hear. "Maybe you're right." I said with a weak smile. "Of course I'm right."

"I guess so."

"Now, let me ask you a question."

"Sure," I said, eager to please.

"Would you like to go upstairs to suck yourself off, or would you rather have me do it?"

My jaw did the trembling thing again. "What did you just say?"

She smiled. "I'm offering to give you a blowjob. But if you'd rather do it yourself, that's fine too."

"You...you will...you'll give me a blowjob?" I said this in a tiny, scared voice.

The right side of her lips curled into a sly smile. "Of course, honey."

The butterflies in my stomach were going crazy. "For real?"

Elaine let her hand rest on my thigh. "For real."

A voice from far way said, "OK". It was my voice, I guess.

"Good! Then let's get you undressed." Elaine helped me to my feet, and I kicked off my shoes, pulled off my socks, tossed my shirt on the chair, and then stepped out of my shorts and boxers.

"I haven't been lonely since my husband died, I have lots of friends, but there's a difference between a friend and a lover. So, I'm a widow looking for a handsome man to play with, and you're a horny young boy who needs an outlet for all that energy you have." Elaine wrapped her long-nailed fingers around my swollen shaft. "I'd say we were a match made in heaven."

She lifted my cock to her lips and I felt her warm mouth engulf me. She slowly deep-throated me, once, twice, a third time. Her kind eyes looked into mine and when she saw me writhe in ecstasy they smiled up at me.

"Ooh."

"Is it as good as when you do it?"

"Better!" It was.

She licked my helmet. "Do you know why it's better?"

"Because you're gorgeous!"

She smiled. "Because it always feels better to have someone else give you pleasure. To share it. That was another reason why your mother brought you here. To make sure you understand that sex isn't just about locking yourself in your bedroom. It's about sharing." She brought my cock back to her lips. "And now I want you to share your hot come with me."

I hadn't jerked or sucked myself in a week, but even if I'd come five seconds earlier I couldn't have lasted long. Watching this attractive older woman look into my eyes as my huge penis slid in and out of her mouth was overwhelming. She of course knew that I like having my ass played with and I felt her fingernails tickle my anus. "It feels good," I whimpered, and a second later I showed her how much I liked it. I came, and it made my most intense autofellatio orgasm look like a dribble. I squeezed my asscheeks together and pumped spurt after spurt of semen down Elaine's throat, and she swallowed every ounce with ease. Her soft, full lips never surrendered their hold on my penis, and her cheeks hollowed as she hungrily sucked every last drop out of my long shaft.

"Oh, honey, that was so good, there was so much come!" I didn't say anything because I was in a fuzzy, happy daze. "Did you like that?" she asked.

"Uh-huh!"

She winked at me. "I knew you would. Now," she stood and helped me to my feet. "Now we have a different kind of fun."

We walked upstairs, Elaine gently holding my floppy penis and leading me along by my cock. She took me to her bedroom, I saw the huge king-sized bed and the black satin bedspread, but we didn't stop there. We went into the bathroom, which its huge, glassed-in shower.

"I'm a bit hurt that you haven't asked me to take my clothes off," Elaine said, pretending to pout.

"Please! I want you to! I do!"

"Well, if you insist," she said with a smirk. "Why don't you get in the shower first and I'll join you. We have to get you nice and clean."

I didn't know exactly why I needed to get nice and clean, but it sounded fine to me. Since my mother ordered me to obey Elaine, obey I did. I twisted the big silver knob and felt the hot spray fill the shower. I stepped in and let the hot jets massage my body. It was delicious, especially after the wonderful thing Elaine did to me. This was not the punishment I expected, but Mother knows best, doesn't she?

I couldn't see clearly through the crazed glass of the shower doors, but I could tell that the bathroom door opened, and I saw Elaine walk in. All I could make out was a curvy pink silhouette coming toward the shower. I was already hugely erect before she even opened the door.

She was gorgeous. Not a hardbody by any stretch of the imagination, and still gorgeous. Her breasts were large and full, and if the sagged a bit under their weight that only inflamed my lust even more. Her nipples were wide and pink and swollen. She had broad, smooth hips and the tiniest roll of soft flesh around her belly. Her skin was smooth and clear, dotted with a few cute freckles on her shoulders. And of course she had that lovely face, smiling mischievously up at me, and those soft hands with their long, sexy fingernails, which reached between my legs and caressed my penis.

I'm not used to getting compliments about my looks and it was nice to hear her say that. I tried to return the favor. "I don't know how anyone could ever resist you."

She kissed me on the cheek. "That's sweet." She took a bottle of liquid soap from a shelf. "Let's get you clean, and I'll show you how irresistible I can be."

For the next ten minutes Elaine's soapy hands and fingers found every sensitive nook and cranny of my body. She washed my armpits, my stomach, my feet, my testicles, my penis. When she filled her hands with creamy soap and wrapped her fingers around my cock and started pumping, pumping, pumping, I thought I would lose my mind.

"I'm gonna come!" I whimpered.

She laughed. "No you won't! I can keep you from coming before I'm ready for it.I can keep you on the brink for as long as I want..." And that's what she did, alternately stroking me like a well-oiled machine and then letting my cock just throb in her hands. This, at last, felt like punishment. But it was the kind I could take for as long as she could dish it out.

"Turn around, honey," she said. I rotated, and she reached around with her left to caress my cock. With the other, she lathered my ass. Her nimble fingers probed me gently, careful not to scratch me there with her fingernail.

"Do you like that?" she asked.

"Yes!" I groaned. Never in my young life had I imagined pleasure so perfect.

"You like my finger up your ass?"

"Yesssss."

"Can I use something else?"

I looked over my shoulder. "What do you want to use?"

She reached for the shelf, moved aside two shampoo bottles, and produced a cylindrical bar of soap. It was sculpted in the shape of a thick, veiny penis, with a big bulbous scrotum.

I said, "Oh, God, yes."

She wet the dildo under the showerhead and then she reached around to take my cock in hand again. Then I felt the slippery head of the soap probe my anus. It was far bigger than the dowel rod I'd used. Elaine took her time inserting it between my cheeks, but when she did it was absolutely incredible. The fat knob forced my sphincter open and then once inside it self-lubricated with every stroke.

Elaine said, "You beautiful boy. It looks so nice sliding in and out between your cheeks."

"It...feels...so...good!"

She kept pushing it into my ass and tickling my cock and I was almost delirious with pleasure. I put my hands on either wall of the shower to keep myself from collapsing. My head lolled back and forth and I wiggled my hips to get the dildo deeper inside me and Elaine's soapy hand up and down my cock.

"I have to come!" I sobbed.

"I know, honey, but not just yet. Isn't this incredible?"

"Yes!"

"Then let's do something I think we're really going to love."

She removed the cock from my ass and released my penis from her tender grip. I groaned. "But I love doing this."

"Trust me. You'll like what I have planned next even better. I know I will."

She dried me with a fluffy towel, but she wouldn't let me touch her. "Not just yet," she said as my hands sought out her breasts. "Can't give away all my secrets at once."

She led me from the bedroom, but we didn't go to the bed as I expected. We walked down a long hallway to the last room on the left.

"You have to understand, my husband and I were married a long time," she said. "We knew what each other liked. We took the time to find out what we both enjoyed. That's important with someone you have sex with, find out what really turns them on."

She opened the door. I looked inside. "Oh, jeez."

It would seem that Elaine and her husband enjoyed a little bit of bondage now and then. I guessed that from the manacles attached to the walls, the straps and restraints lying on the table by the bed, and from the bed itself, which looked like something that might have been used on infidels during the Inquisition. It had a metal framework built around it, chains hanging from the metal struts, and all sorts of weird collars and pulleys that I couldn't figure out and didn't really care to.

"Go on," Elaine said. "Climb on the bed."

"I, uh, I don't know."

"Honey," Elaine said, "if you don't do exactly as I say, and your mother finds out, well, it's going to be very unpleasant for you. I promise you'll love what I'm going to do to you. I doubt you'll be so lucky with your mom."

What choice did I have. "What do I have to do?"

"Get on the bed and lie down." I did. "Put your legs in these collars." I did. "Your wrists, put them in these restraints." I did. I didn't want to, but I did.

"Don't you just look delicious," she said. She leaned down and kissed my stomach, my nipple, my lips. "Have you had fun so far?"

"Yes."

"Now I'm going to have some fun."

Elaine walked to the head of the bed, where I could only see her in my peripheral vision. "Now I'm going to find out just how flexible you are." There was a winch, and she slowly turned it. The metal thread that held the restraints tightened, tightened, until they lifted my legs up off the bed. She cranked until my legs were over my head, my ass in the air, my cock in my face.

"What are you doing?" I said, trying to keep the strain out of my voice.

"I want to see your technique. I want to see how well you give head."

"I thought I wasn't supposed to do that anymore."

She smiled down at me. "You're supposed to do whatever I say."

I leaned forward to capture my glans in my mouth. "Should I make myself come?"

"Do your best."

It was hard because I couldn't use my hands, but I sucked my big head into my mouth and went to work. I bobbed my head up and down as far as I could, swirling my tongue like mad, doing everything I could to make myself come. I needed to come so bad.

"Feel good, honey?" Elaine said.

"Umph! Um-hmm!"

"Then how does this feel?"

I sensed her moving down between my legs. And then, oh my God, I felt her tongue burrow into my puckered asshole. "Huhhh!" I groaned. It was absolute heaven, I had my cock in my mouth, and Elaine's wet tongue rimming my anus. She pulled my sphincter open with her fingers and drove her tongue deep inside me. I sucked faster and faster on my cock, not caring at how dirty and weird this situation was, just wanting to COME so bad.

"Are you going to come, honey!" Elaine said.

"Uhhh!"

"Do you want to come, babydoll?"

"UHHHH!!!"

"Then go ahead."

I sucked, she licked, I sucked and sucked and sucked and I felt the big plum in my mouth swell as my orgasm burst. It felt so good to have my cock in my mouth but if felt so much better with Elaine's darting tongue ravaging my rectum. I pulled my mouth away for just a second. "CUMING!" I gurgled.\

Elaine leapt up from between my legs and crawled beside me. My penis finally erupted and she seized my cock and held it as my come flowed into my mouth. After a few spurts she pulled my penis free and capped her own mouth over the tip, drinking me down. Then she leaned down and kissed my lips, her come-coated tongue caressing my own.

"Tastes so good," she moaned.

"It feels so good."

"Don't you love feeling it shoot in your mouth?"

I hated to admit it, but, "Yes."

"It feels any better when it comes inside you. You'll never know what that feels like. Even you can't twist yourself into position to get that big cock up your ass."

"No, I don't think so."

I was exhausted. Elaine seemed to sense this, because she went to the winch and cranked me down. But not all the way. My legs were still high in the air, splayed open, my cock and balls and ass still totally exposed.

Elaine walked around me, again letting her sexy nails scrape all over my body. "Aren't you letting me down?" I asked.

She laughed. "Oh, no. So far you've had all the fun. Now it's my turn." Maybe it was me, but her tone sounded ominous.

She went to a closet against the far wall and opened to big wooden doors. I couldn't see what she was doing behind it, but it looked like she was putting something on.

"Honey?" she called.

"Yes?"

"You think I'm attractive, don't you?"

"Oh my God, yes!"

She giggled. "You think I'm...hot?"

"Yes."

"Danny, do you want to fuck me?"

I couldn't believe it. Was I going to lose my cherry? I'd come twice already but I definitely had another load in me. "I'd LOVE to!"

"Well, in that case, then I guess you won't mind if I fuck you first."

She closed the closet door. Elaine stood there wearing some kind of harness with black leather panties. I looked between her legs, and sticking out from those panties was a long, pink dildo that had a huge scrotum hanging down.

"Oh my God!" I cried.

"Your mother said she was going to make you cry for help," she giggled. "I think about what she had in mind."

"Oh, no, no!"

"You'll love it, honey." Elaine said as she advanced on me. She had a big tube of lubricant in her hand. "You'll love it."

She reached down and it seemed like she flipped a switch. Sure enough, I heard a faint buzzing, and a blissful smile spread over her lips. "See, that hits me in just the right spot. Every time I thrust, that makes me feel very, very good. So we both get to have fun."

I was scared but I was more excited. "Please!" I wasn't sure if I meant, "Please, no!" or "Please, fuck me!"

It didn't matter. Elaine crawled between my legs and smeared the cool lube all over my anus, sliding her finger deep inside me. She applied the slippery stuff to the big pink dildo, and she grabbed my hips and started sliding the superhard probe into my ass.

"When you met me, you thought I was just a sweet, innocent old lady, didn't you?"

"Yes!" I moaned as my anus was stretched further than ever before.

She pushed forward until all six pink inches were inside me. I felt the faint buzzing of the vibrator that doubtless was exciting her clitoris. "Well, honey, I think you've figured out by now that I'm a little bit wild."

To prove her point she grabbed my hips and started fucking me. Not too hard, not too fast, but hard enough and fast enough that I shrieked with pleasure. It was humiliating, strapped to a bed and getting penetrated by a 50-year old woman, but I didn't care. It felt so incredible that I screamed, "Fuck me! Fuck me up the ASS!"

"Feel good?" Elaine asked.

"Yes!"

"Want to feel even better?"

"Yes, yes!"

She paused long enough to fill her hands with the lubricant. Then she wrapped her fingers around my cock and started jerking me off as she fucked me.

I lost control of my body. I floated on a cloud on pure ecstasy. Her long-nailed fingers stroked my cock, her big pink cock pumped in and out of my asshole, I looked up and saw Elaine's kind, gentle face smiling down at me.

She closed her eyes and moaned. "Oh, honey, I think I'm gonna come." She fucked me faster, faster. "Oh, honey, yes, yes!" She tightened her grip on my cock and used my dick and an anchor so she could fuck me harder. The buzzing vibrator hit just the right spot and her full lips split into a huge grin.

"You know how I said you'd never feel someone come inside you?" she said.

"Uh-huh."

Her mouth fell open. "Well, I hope you enjoy this." She released my cock, drove herself deep inside me, and she reached down to grab the big testicles swinging below the shaft. She squeezed them, and I felt something liquid and warm ooze into my rectum. There must have been some kind of creamy goo in there and Elaine shot it up my ass. "Come in, me, uhh, Elaine! Come in me!"

When she was done, she took hold of my slippery cock and started on me again. "Do you have one more in you?" she teased.

"Oh, at least."

"That's all we have time for today, honey." She put more lube on my cock and started stroking me with both hands. She greased up my huge shaft and pumped me so hard she was bouncing up and down on the bed, and that made the big pink dick in my ass wiggle deliciously.